Benefits Specialist

If you have an interest in being part of one of the fastest growing industries in the nation in you may consider wanting to work for Trulieve! If you have a desire to help others in need through your efforts, this may be the role for you!

At Trulieve, we strive to bring our patients the relief they need in a product they can trust. Our plants are hand-grown in an environment specially designed to reduce unwanted chemicals and pests, keeping the process as natural as possible at every turn.

Our products are designed to alleviate seizures, severe and persistent muscle spasms, pain, nausea, loss of appetite, and other symptoms associated with serious medical conditions such as cancer.

Our specially trained staff works hand-in-hand with physicians to provide the right products and the correct dosage to ensure patients get the compassionate care they need.

To learn more about our company, please visit our website;

Requisition ID: 17327

Remote Work Available: No

Job Title: Benefits Specialist

Department: Human Resources

Reports to: Sr. Benefit Manager

Role Summary

The Benefits Specialist administers health & welfare and retirement programs, serves as a subject-matter resource for FMLA/ADA leave and accommodation cases, and performs accounting reconciliations related to benefits billing, payroll deductions, and vendor invoices. This role will partner closely with HR, Payroll, Finance, and third-party administrators to deliver seamless employee experience and ensure compliance with federal and state regulations.

Key Duties And Responsibilities

Core Benefits Administration (60%)

• Administer day-to-day operations of medical, dental, vision, HSA/FSA, life/AD&D, disability, COBRA, EAP, and retirement plans.
• Manage eligibility events (new hires, QLEs, life-event audits), enrollments, terminations, and data loads between HRIS, payroll, and benefit carriers.
• Provide tier-2 employee support, resolving complex coverage and claims escalations with carriers/TPAs.
• Coordinate annual open enrollment: timelines, testing, communications, rates, plan setup, and post-OE audits.
• Maintain plan documents, SBCs, and intranet content, draft employee communications, and FAQs.
• Track and audit payroll deductions; research discrepancies across HRIS, payroll, and carrier files.
• Support wellness initiatives.
• Answer all incoming tickets and handle inquiries whenever possible or redirect as appropriate
• Assist in the planning and preparation of meetings, conferences, and conference calls
• Maintain a friendly and professional demeanor and be quick to offer assistance or support as often and as regularly as needed

FMLA/ADA Case Management (25%)

• Act as a primary point of contact for FMLA and company leave programs; ensure accurate eligibility determinations, notices, tracking, and return-to-work coordination.
• Lead ADA interactive process: intake, documentation, essential functions review, accommodation analysis, approvals/denials, and follow-up.
• Partner with managers, Safety, and Legal on complex or overlapping cases (e.g., workers' comp, state leave, ADA).
• Maintain meticulous case files and confidentiality; ensure timely communication and legally compliant documentation.
• Monitor regulatory changes; recommend policy/process updates and manager education.

Accounting Reconciliation & Controls (15%)

• Perform monthly benefits invoice and premium reconciliations against payroll deductions and eligibility files; prepare variance explanations and submit for approval.
• Track retroactivity (new hires, QLEs, terminations), coordinate refunds/collections, and post journal entries in partnership with Finance.
• Support 401(k)/retirement plan funding confirmations and withdrawal deduction audits to ensure continuous compliance.
• Maintain reconciliation checklists, process narratives, and control evidence for audit readiness (internal/external).

Compliance & Reporting (shared across duties)

• Assist with ERISA/ACA/COBRA compliance, Section 125, HIPAA privacy, and nondiscrimination testing.
• Contribute data and documentation for ACA reporting (1094/1095), annual Form 5500 filings, and nondiscrimination tests.
• Prepare routine and ad-hoc reports (enrollment, leaves, costs, trends, KPIs); ensure data integrity and version control.

Skills And Qualifications

• Leads with empathy and provides solution-oriented support.
• Attention to detail for reconciliation, audit trails, and SOX-aligned discipline.
• Possesses high integrity to make sound decisions with private health information and personnel data, in accordance with HIPPA regulations and standards.
• Excellent communication skills for cross-department collaboration with HRBP, Payroll, Finance, and Legal.
• Possesses a continuous improvement mindset to document processes and propose efficiency gains.
• Possess computer proficiency, speed, and knowledge of Microsoft Office Suite and SharePoint
• Excellent organizational, communication, and interpersonal skills, both written and oral, Bi-lingual (Spanish) preferred
• Self-driven and able to manage multiple and changing priorities with little direction and supervision.
• Strong problem-solving and decision-making skills with the ability to develop multiple solutions to an issue and make valid recommendations for resolution.
• Ability to prioritize, manage time appropriately, and multitask under pressure.
• Ability to learn new tasks quickly.
• Self-motivated attitude with excellent work ethic.

Additional Minimum Qualifications

• High School Diploma required, AA or BS Degree (Preferred). Experience instead of degree will be considered.
• 3-6 years relevant experience, preferably in HR with FMLA, ADA, Benefits, and HRIS experience
• 3-6 years of data analysis experience preferred.
• 1-2 years of exposure to accounting reconciliation or payroll/benefits accounting tasks.
• Certifications (preferred): SHRM-CP or Certified Leave Management (CLMS/CLM)
• Must possess a valid driver's license and good driving record.
• Must be a minimum of 21 years of age.
• Must complete a comprehensive background screening. *

Physical Requirements

• Must be able to push, pull, move, and/or lift a minimum of 25 lbs. to a minimum height of 5 feet and able to push, pull, move, and/or carry such weight a minimum distance of 50 feet, with or without mechanical assistance
• Must be able to work seated/standing as appropriate at workstations for extended periods of time, maintain body equilibrium while climbing ladders, stairways, stopping, kneeling, crouching, and reaching, and use hands/fingers to hold, grasp, turn, pick, pinch frequently/constantly to complete tasks.
• Must have visual acuity with/without job aids to perform activities such as reading, viewing a computer terminal, visual inspection involving small parts/details. Clarity of vision at 20 ft or more in day and night/dark conditions
• Must be able to speak and communicate verbally at conversation levels with co-workers, vendors, etc. (Moderate noise)

WORK SCHEDULE

• 40+ hours weekly with flexible hours depending on department needs. Must be available to work occasional evenings, weekends, and holidays.
• Occasional extended hours during open enrollment, year-end or audits.
• Salary will be commensurate with experience. A comprehensive benefits package including paid time off is offered with this position.
• Equal Opportunity Employer l Trulieve Supports a Drug Free Workplace

Salary will be commensurate with experience. A comprehensive benefits package including paid time off is offered with this position. This position will work an average of 40 hours per week and will be available "after hours" if an emergency situation should arise.

Trulieve provides equal employment opportunities to all employees and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, pregnancy or any other characteristic protected by federal, state or local laws.